


Retrospective In The Future

by red_crate



Category: Teen Wolf (TV)
Genre: Additional Warnings In Author's Note, Alternate Universe - College/University, Alternate Universe - Human, Anal Fingering, Anal Sex, Condoms, Cunnilingus, F/M, Hook-Up, Hopeful Ending, M/M, Rimming, Threesome
Language: English
Status: In-Progress
Published: 2018-09-17
Updated: 2018-09-17
Packaged: 2019-07-13 16:45:35
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,640
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16021928
Author URL: https://archiveofourown.org/users/red_crate/pseuds/red_crate
Summary: Lydia told Stiles in their direct messages that Jackson was a bit of a cockslut when he has the opportunity. That's how the whole thing started anyway: Stiles answering the tinder ad of a couple looking for a guy to hook-up with.





	Retrospective In The Future

**Author's Note:**

  * For [TamerOfPickles](https://archiveofourown.org/users/TamerOfPickles/gifts).



> This is for Ryan, who asked for "Jackson and Lydia discovering that Jackson likes to bottom, so Lydia gets guys (in this case Stiles) to top Jackson while she watches." I really hope I hit a tone you enjoy for this dynamic. It got a bit more emotionally messy than I initially planned. 
> 
> Additional note: Stiles doesn't have sex with Lydia in this fic, but they do make out.

 

Buzzed and feeling relaxed, this whole idea is starting to seem less outlandish and more like closure of sorts. Stiles didn't have a terrible high school experience, but the hands trailing over his body and the mouths slanting together next to him did their fair share of damage back then. He pushes Jackson's pliant form up against the wall now and nips at an exposed collarbone.

“Seventeen year-old me would shit a brick if he knew this is where I'd end up.” Stiles’ mouth runs away from him as he trails kisses along Jackson's neck. 

Lydia has the apartment door open and a finger crooked in one of Stiles’ belt loops before Jackson has time to react with more than a choked snort. “This way, boys.” She tugs Stiles along and threads the fingers of her other hand with Jackson's until the three of them stumble into the small entrance. As soon as she releases them, Lydia is tugging off the simple, dark green dress she wore tonight. Miles of supple, creamy skin on display— everything Stiles used to limit himself to dreaming of back in high school. Her heels get kicked off, and she turns to face them again, looking like the world's sexist naked cruise director. “Bedroom.” 

Jackson’s dress shirt is a mess of wrinkles from where Lydia helpfully unfastened the top three buttons during their Uber from the bar. Stiles made it worse, getting handsy and figuring out Jackson likes his nipples played with. At least Lydia promised a good review to the driver and tipped one hundred percent. He's pretty sure the dude hadn't enjoyed the moaning in the middle of his backseat. 

Stiles is taller than Jackson now and broader in the shoulders than he was back in high school. He takes advantage of it by walking right up against him and putting his hands on Jackson's slender waist. A vision of them naked and slamming into Jackson from behind blazes across Stiles’ mind momentarily. He tugs the shirt free from the restriction of Jackson's jeans, seeking warm skin. His fingers slot against the shallow cut of his hips, squeezing.

“Fuck,” Jackson's voice wavers, breathy. He hesitates on his next step and leans back against Stiles. The motion brings some much appreciated pressure against Stiles’ throbbing cock. 

Lips grazing Jackson's ear, Stiles chuckles and says, “That's the plan, big boy.” He slips his hand down the front of Jackson's jeans for emphasis, cupping the bulge he finds. 

When they get to the bedroom, Lydia reaches for him, arms winding up and pulling him down into a kiss. It's surreal, less believable than the fact that he's spent the last twenty minutes making out and groping his high school bully. She smiles sweetly when they part, eyes dark and makeup barely smudged. “I'm really glad it ended up like this. I always liked you.  _ We _ always liked you.” She glances significantly over at Jackson who is busy not looking at them as he gets his sneakers and jeans off. When she meets Stiles’ eyes again, she explains, “Repression.” 

That doesn't fix the hurt and confusion Stiles went through, but it's not like he's spent the last four years dwelling on it. He assumed as much on his own anyway, but it's a nice olive branch, he guesses. 

Stiles smiles back at her, lips starting to chap already. “We all had stuff going on.” 

“Are we going to do anything  _ now _ ?” Jackson interjects, clearly uncomfortable with the topic or maybe just the fact that they're talking and not  _ doing. _

Lydia told Stiles in their direct messages that Jackson was a bit of a cockslut when he has the opportunity. That's how the whole thing started anyway: Stiles answering the tinder ad of a couple looking for a guy to hook-up with. Jackson apparently really liked being fucked. 

Stiles pulls away from Lydia and all his dormant, teenage daydreams. He crosses the few feet of space between them and shoves Jackson down onto the bed, grinning. “You want something, Jackson?” Stiles heard the sharp, interested sound Lydia made. 

A blush stretches over Jackson's smooth chest and up his neck. That frown of irritation Stiles is still familiar with after all this time graces Jackson's beautiful features. But then his eyes are slipping shut, and he's arching up with a nod. This is not a reaction Stiles knows from him, but it's better for it. Stiles reaches out, wrapping his hand lightly over Jackson's throat. He can feel Jackson freeze, pulse beating hard against his fingertips. He feels the moment when Jackson lets go, gives in and relaxes into vulnerability. 

For the first time, Stiles thinks this is really going to work. He can have this and enjoy it even with the ghost of the past lurking in the shadows. 

“He likes being pushed around a little,” Lydia says from where she's draped herself on the bed next to them. When she cups her hand over Jackson's bicep, he lets out a breath. 

Stiles looks between them, at the well worn familiarity and maturity they've grown into. If she'd tried volunteering that info back when they went to school together, Stiles is pretty sure they'd be broken up for a good week or two. 

Withdrawing, Stiles sits up on his knees and pulls off his shirt. Time to get this show on the road. As he unzips his jeans and works them down, he tells Jackson, “Roll over. You should make her feel good while I get you ready.” 

Jackson does as he's told and maneuvers until he's positioned between Lydia’s thighs. Stiles gets lost watching Lydia slide her fingers through the soft hair at the back of Jackson's head as he mouths along her cunt. Soft sounds of kissing and licking are covered by the breathy little gasps Lydia starts to make. They're beautiful together. 

Stiles strokes where he's gone half hard, firming up all over again as he visually traces along each curve and plane they make. With his other hand, Stiles squeezes one of Jackson's ass cheeks and pulls until his entrance is exposed. The soft skin there dusky and smooth just like everywhere else on Jackson's body. 

“Do you wax everything?” Stiles asks even though he shouldn't.  He runs the pad of his thumb over the tight ring of muscle, testing the resistance. 

Lydia chuckles, but it's cut off with a moan when Jackson tongues her clit over and over. “Are you complaining?” 

Stiles meets her heady gaze over Jackson's shoulder as he leans down to lick a broad stripe from Jackson's balls up over and around his hole. “Nope.” He uses the tip of his tongue to circle around the sensitive area, staying longer than he had planned once Jackson groans and shoves his ass backwards. 

Stiles likes this, likes making his partners feel good. Something darker and childish inside fills with satisfaction at making Jackson Whittemore whine for more. He goes for it hard, licking and pushing with his tongue until Jackson is cursing and moaning right up against Lydia’s core.  

“God, yes,” she groans, pushing Jackson away. When Stiles looks up, she's lying against the pillows, staring at them hard as she works herself with two fingers fucking in and out. “Fuck him, Stiles.” 

The lube and condoms were sitting on the bedside table within easy reach when they got inside. Stiles snatches the small bottle and flicks the lid open. He's throbbing now, high on the power trip from having Jackson writhe against his tongue. 

He gets a fingertip inside Jackson's ass where it's hot and welcoming. Then two and he's spreading them, fucking in and out as slowly as he can when he's feeling so desperate to get his cock inside. 

“Come on,” Jackson demands, head turned to the side and eyes screwed shut. He pushes up onto his elbows. “Come on.” 

Stiles wants to. He wants to push inside and ride Jackson hard, make him feel it even after Stiles is gone. Instead, he works a third finger inside and searches for that sweet spot. “Impatient.” 

Jackson collapses onto his chest, and Stiles watches his knuckles turn white when he claws at the sheets as Stiles works him over. 

It's not until Jackson sobs out, “Stiles, please!” That Stiles pulls his wet fingers free and wipes the lube off on Jackson's lower back. 

He gets the condom on in record time, rolling it on and checking the reservoir before lining up. Jackson goes still in anticipation as Stiles pushes in carefully. It's so fucking good. He grinds in even after he's all the way seated. 

“That what you want?” He asks before biting his lip and pulling back to snap back in. “You want my cock, Jackson?”

“Yeah. Yeah, c'mon, fuck me,” Jackson pants out, rocking back and forth in the rhythm Stiles set. His knees are spread wide, ass up and so clearly wanting anything and everything Stiles will give him. 

Watching the place they meet, Stiles can't help but groan. He left a smattering of beard burn from his patchy stubble, and Jackson's hole is stretched wide around the girth of his cock. It's mesmerizing, only makes the need Stiles feels building that much more acute. He has to look away or he'll come too soon.

Lydia has pulled a silky looking throw blanket over her legs, and she looks sated. Stiles feels bad for missing her climax, though she seems perfectly happy to just watch. When she catches his eye, the smile she gives him would fit a cat who got the cream. 

Stiles pushes down on Jackson's back, rolling his hips faster and hoping this looks as hot as it feels. His hand starts to slide in the sweat on Jackson's skin. He slams into Jackson, mouth going dry as he pants. 

“Stiles. Stiles,” Jackson whines over and over, reaching down to touch himself. 

Stiles feels the brush of Jackson's fingers where he's reached all the way back to touch the place they join. Both of them moan when Jackson traces the bottom of his own rim.

“Fuck,” Stiles curses, pulling out. “Flip over. I wanna see how much you want it, slut.” The world rolls out of his mouth easily, leaving him feeling hot all over at the way Jackson squirms and curls into himself for a split second before turning onto his back. 

“Don't call me that,” Jackson demands.

When Stiles looks over at Lydia, she nods. She doesn't look offended or angry on Jackson's behalf. It's part of the game, he guesses. 

Stiles presses forward to kiss Jackson and bite at his lip. Parting just enough the speak, Stiles rubs his cock against Jackson's ass. “It’s what you are, isn't it? A slut?” 

Jackson's expression goes pained, and he whimpers a little, but he's also clutching at Stiles and pulling him closer. 

Stiles starts to slide back inside Jackson. He mouths along the heated skin of his cheeks. “It's okay,” Stiles says, “I like it. I want you to beg for it, for my cock.” 

Jackson moans, nails digging into Stiles’ back as he continues talking all while shallowly fucking him. 

“When Lydia showed you my dick pic, did your mouth start to water? Did you think about what it would feel like to sit on it?” Stiles isn't even sure what he's saying, just talking and spouting off whatever feels sexy. “Could have done this back in high school, Jax. Coulda fucked you in the locker room. Who knew all that anger was because you just needed a good dicking?”

Stiles leans back and pushes Jackson's knees farther apart where they've been spread around his chest. The guy is still athletic and flexible. Stiles fucks in hard and deep, pushing a groan straight out of Jackson. 

The way Jackson whines _ “Yes” _ , dragging the word out into a high pitched whine goes straight to Stiles' balls. 

He's going to be thinking about this a lot when he's in his own bed and feeling a little lonely. 

Stiles fucks him in earnest now, caring less about finesse and more about getting off. He’s been horny since he started getting ready for their meet up, and the three of them spent too long at the bar talking and touching each other furtively. Now that he's here balls deep in Jackson, it's difficult to think past chasing the climax. 

Everything feels too good. 

“You're so good at this,” Stiles groans. He tips his head back, overwhelmed by the way Jackson just takes each thrust so eagerly, pressing up to meet him. “God, I want to...” He bites his words off, moaning.

He was going to say  _ “I want to fuck you over and over.” _ But that isn't the deal, and Stiles is cool with it. 

Jackson arches back, moaning and groaning as he strokes himself off. His cock is curved slightly, cut, and pretty. Stiles hopes he gets the chance to suck him off later, taste the precome before letting him come on his face, maybe. 

“Fuck yeah. Come on my dick,” Stiles demands. He keeps the angle he's been hitting, enjoying the way Jackson’s cock drools precome against his own stomach. 

The spasm of Jackson's orgasm makes Stiles groan and lose his balance. He slumps forward, pounding into Jackson with abandon and hoping it's okay. His own climax crashes through his body like a bolt of lightening right on the heels of Jackson's.  

The warm, slick slide between their stomachs where Jackson's softening cock is trapped feels oddly nice. Stiles turns his head to press his face against Jackson's shoulder, breathing in the thick scent of sex as he recovers. 

When Jackson's legs slip down to hook over the back of his knees, Stiles sighs happily. “That was fun.” 

Jackson makes an agreeing sound, then says, “You're heavy.” 

That pulls a snort from Stiles. Some things don't change, he guesses. But he carefully holds the condom in place before pulling out and rolling off. He's sweaty, a little winded, and feeling like he's made of goo. 

Lydia crawls over Jackson and they kiss for several minutes. Stiles watches from what feels like a distance, thinking about how good of a fit they still are for each other even now. He watches the soft smile Lydia gives Jackson when they part, the way Jackson tucks her hair back softly. 

He looks away, starting to sit up so he can get rid of the condom. Lydia beats him though, cupping his jaw and pulling him into a kiss of their own. It's good. It makes Stiles sigh happily even when he's starting to feel a little like a caged animal in the aftermath. 

She reaches over and plucks a handful of tissues from the box on the nightstand. “Let me,” she asks almost shyly. 

When Stiles nods, dazed, she uses the tissues to wrap up and slip off the condom. She tosses that into the trash before grabbing a couple more tissues and wiping any excess lube off his groin, paying mind to his hypersensitive cock. 

“Thanks?” Stiles doesn't know what to say, has never had an experience like this— hooking up with old classmates and having the person he  _ didn't  _ fuck clean him off. “This was...” Stiles searches for the right word as he watches Lydia shimmy back to the other side of Jackson. One word keeps coming to mind however inadequate as it feels with all his mixed up emotions. “Nice. This was nice.” 

Jackson nods, staring up at the ceiling before looking over and meeting Stiles’ eyes. “Yeah. It was.” 

An amused chuckle filters over from Lydia, and she grins at Stiles when he looks over at her. 

Lying back down since no one seems to be in a hurry to get him out of there, Stiles agrees with himself. 

_ This was nice.  _

 

**Author's Note:**

> If you wanna come hang out with me on Tumblr, I'm [here](http://the-redcrate.tumblr.com).
> 
> Comment if you enjoyed this, please!


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